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WO1997004808A1 - Compositions contenant des analgesiques et des antihistaminiques et procedes de traitement d'affections respiratoires - Google Patents

Compositions contenant des analgesiques et des antihistaminiques et procedes de traitement d'affections respiratoires Download PDF

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Publication number
WO1997004808A1
WO1997004808A1 PCT/US1996/012249 US9612249W WO9704808A1 WO 1997004808 A1 WO1997004808 A1 WO 1997004808A1 US 9612249 W US9612249 W US 9612249W WO 9704808 A1 WO9704808 A1 WO 9704808A1
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WO
WIPO (PCT)
Prior art keywords
composition according
pharmaceutical composition
group
methyl
pyrrolidine
Prior art date
Application number
PCT/US1996/012249
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English (en)
Inventor
Ronald Dean Cramer
Sekhar Mitra
Donald Kay Riker
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP9507747A priority Critical patent/JPH11510168A/ja
Priority to AU65991/96A priority patent/AU6599196A/en
Priority to EP96925495A priority patent/EP0841947A1/fr
Publication of WO1997004808A1 publication Critical patent/WO1997004808A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents

Definitions

  • the present invention relates to compositions and methods for providing improved treatment, management or mitigation of cold, cold-like, allergy, sinus and/or flu symptoms by administering a safe and effective amount of a composition comprising an analgesic agent along with certain pyrrolidine and piperidine ether antihistaminic agents.
  • the common cold although not usually a serious illness, is a highly pre ⁇ valent, discomforting and annoying affliction.
  • the term "common cold” is applied to minor respiratory illnesses caused by a variety of different respiratory viruses. While rhinoviruses are the major known cause of common colds, accounting for approximately 30 percent of colds in adults, viruses in several other groups are also important. While immune responses occur, and infection with some respiratory tract viruses therefore could be prevented by a vaccine, development of a polytypic vaccine to cover all possible agents is impractical. Thus, the problem of controlling acute upper respiratory disease presents complex challenges, and the long-desired discovery ofa single cure for the common cold is an unrealistic expectation.
  • the costs of treating colds with over-the-counter medications in the United States is estimated at an annual cost of over l.S billion dollars.
  • the direct costs of treatment in outpatient clinics is estimated at almost four billion dollars. Indirect costs, based on the amount of loss in wages because of restricted activity are substantially higher.
  • Exemplary prior art formulations for treatment of cough, cold, cold-like, allergy, sinus and/or flu symptoms and the discomfort, pain, fever and general malaise associated therewith generally contain an analgesic (aspirin or acetaminophen) and one or more antiWstaminics, decongestants, cough sup ⁇ pressants, antitussives and expectorants.
  • analgesic aspirin or acetaminophen
  • non-steroidal anti-inflammatory drugs to combat inflammation and attendant pain is accepted medical practice.
  • the non-steroidals are commonly employed to relieve pain and inflammation associated with, for example, bursitis, arthritis, headache and the like.
  • drugs of the non-narcotic analgesic class of drugs are aspirin, acetaminophen, ibuprofen, ketoprofen, diclofenac and naproxen and their salts (e.g., lysine, arginine, sodium and potassium).
  • Aspirin, acetaminophen and ibuprofen have heretofore been includ ⁇ ed as the pain reliever and fever-reducing component in conventional cough/cold multisymptom alleviating compositions.
  • These commercially marketed products generally contain in addition to aspirin, acetaminophen or ibuprofen, one or more antiMstarninics, decongestants, cough-suppressants, antitussives and expectorants.
  • compositions comprising an analgesic agent along with certain pyrrolidine and piperidine ether antihistaminic agents provides improved treatment, management or mitigation of cold, cold-like, allergy, sinus and/or flu symptoms, including nasal congestion.
  • symptoms refer to coryza, nasal congestion, sinus congestion, sinus pain, upper respiratory infections, otitis, sinusitis, etc.
  • the present invention relates to compositions and methods for providing improved treatment, management or mitigation of cold, cold-like, allergy, sinus and/or flu symptoms by administering a safe and effective amount of a composition consisting essentially of an analgesic agent along with certain pyrrolidine and piperidine ether antihistaminic agents.
  • the present invention relates to compositions and methods for providing improved treatment, management or mitigation of cold, cold-like, allergy, sinus and/or flu symptoms by administering a safe and effective amount of a composition consisting essentially of an analgesic agent along with certain pyrrolidine and piperidine ethers.
  • Useful analgesic pharmaceutical actives in the compositions of the present invention include aspirin and acetaminophen as well as the non-steroidal anti-in ⁇ flammatory drugs (NSALDS) selected from the following categories: propionic acid derivatives; acetic acid derivatives; fenamic acid derivatives; biphenylcarboxylic acid derivatives; and oxicams. All of these NSALDS are fully described in the U.S. Patent 4,985,459 to Sunshine et al., issued January 15, 1991, incorporated by refer ⁇ ence herein.
  • NSALDS non-steroidal anti-in ⁇ flammatory drugs
  • Examples of preferred analgesic pharmaceutical actives useful in the present invention include, but are not limited to, acetaminophen, acetylsalicylic acid, ibupro ⁇ fen, fenbuprofen, fenoprofen, flurbiprofen, indomethacin, ketoprofen, naproxen, their pharmaceutically-acceptable salts, enantiomers thereof) and mixtures thereof.
  • Acetaminophen, ibuprofen and naproxen are especially preferred for use in the compositions ofthe present invention.
  • salts refers to salts prepared from pharmaceutically acceptable non-toxic bases including inorganic bases and organic bases. Salts derived from nonorganic bases include sodium, potassium, lithium, ammonia, calcium, magnesium, ferrous, zinc, manganous, aluminum, ferric, manganic salts and the like.
  • Salts derived from pharmaceutically acceptable organic non-toxic bases include salts of primary, secondary, tertiary and quaternary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion exchange resins, such as triethylamine, tripropylamine, 2-dimethylaminoethanol, 2- diethylaminoethanol, lysine, arginine, histidine, caffeine, procaine, N-ethylpiperidine, hydrabamine, choline, betaine, ethylenediamine, glucosamine, methylglycamine, theo ⁇ bromine, purines, piperazine, piperidine, polyamine resins and the like.
  • basic ion exchange resins such as triethylamine, tripropylamine, 2-dimethylaminoethanol, 2- diethylaminoethanol, lysine, arginine, histidine, caffeine, procaine, N-ethylpiper
  • acetaminophen and the S(+) isomer of the NSAIDs and their salts.
  • S(+) H as applied to the analgesic agents herein is intended to encompass the dextrorotatory or S(+) isomer of the amino acid salt derivatives thereof.
  • substantially free ofthe R(-) antipode as used in conjunction with the term “S(+)” means that the S(+) enantiomer is sufficiently free of its R(-) antipode to exert the desired onset-hastened and enhanced analgesic effect.
  • the active ingredient should contain at least 90% by weight of the S(+) enantiomer and 10% or less weight R(-) enantiomer.
  • the weight ratio of S(+) enantiomer to R(-) enantiomer is greater than 20:1, more preferably greater than 97:3.
  • the S(+) enantiomer is 99 or more % by weight free of R(-) enantiomer, i.e., the weight ratio of S to R is approximately equal to or greater than 99: 1.
  • the safe and effective amount of ibuprofen used in the compo- sitions of the present invention generally ranges from about 50 to about 800 mg, preferably from about 50 to about 400 mg and more preferably from about 50 to about 200 mg.
  • the safe and effective amount of naproxen used in the compo ⁇ sitions of the present invention generally ranges from about 50 to about 660 mg, preferably from about 100 to about 330 mg and more preferably from about 150 to about 220 mg.
  • the safe and effective amount of flurbiprofen used in the compositions of the present invention generally ranges from about 12.5 to about 300 mg, preferably from about 12.5 to about 200 mg, more preferably from about 12.5 to about 100 mg and most preferably from about 12.5 to about 50 mg.
  • the safe and effective amount of ketoprofen used in the compositions of the present invention generally ranges from about 5 to about 100 mg, preferably from about 5 to about 75 mg, more preferably from about 5 to about 50 mg and most preferably from about 5 to about 25 mg.
  • the amount of the S(+) isomers of these agents will be about half of the amount ofthe racemic mixture.
  • R ⁇ is a radical selected from the group consisting of hydrogen, halogen, lower alkyl containing from 1 to 4 carbon atoms and lower alkoxy containing from 1 to 4 carbon atoms
  • R2 is a radical selected from the group consisting of lower alkyl containing 1 to 4 carbon atoms
  • n is an integer from 0, 1, 2 and 3 and n is an integer from 1 to 2, with the proviso that +n must be at least 2. Salts of these compounds are also useful.
  • Most preferred for use herein is N-methyl-2-[2'( ⁇ -methyl-p-chloro- benzhydryl-oxy)ethyl]-pyrrolidine which is commonly known as clemastine fumarate and sold as Tavist® by Sandoz Pharmaceuticals.
  • the safe and effective amount of these pyrrolidine and piperidine ethers gen ⁇ erally ranges from about 0.1 to about 10 mg, preferably from about 0.3 to about 3 mg, more preferably from about 0.5 to about 2 mg and most preferably from about 0.67 to about 1.34 mg.
  • compositions ofthe present invention can also include at least one other pharmacological active selected from the following class: (a) a decongestant, (b) an expectorant (c) an additional antihistamine and (d) an antitussive.
  • the decon- gestants useful in the compositions of the present invention include pseudoephed- rine, phenylpropanolamine, phenylephrine and ephedrine, their pharmaceutically ac ⁇ ceptable salts, and mixtures thereof.
  • antitussives useful in the present invention include those such as dextromethorphan, chlophedianol, carbetapentane, caramiphen, noscapine, diphenhydramine, codeine, hydrocodone, hydromorphone, fominoben, their pharmaceutically-acceptable salts, and mixtures thereof.
  • the additional antihistamines useful in the present invention include those such as chlor- pheniramine, brompheniramine, dexcWorphen amine, dexbromphreniramine, tripro- lidine, azatadine, doxylamine, tripelennamine, cyproheptadine, hydroxyzine, car- binoxamine, phenindamine, bromodiphenhydramine, pyrilamine, their pharmaceuti ⁇ cally acceptable salts, as well as the non-sedating antihistamines which include acrivastine, AHR-11325, astemizole, azatadine, azelastine, cetirizine, ebastine, ketotifen, lodoxamide, loratidine, levocabastine, mequitazine, oxatomide, setastine, tazifylline, warmthlastine, and terfenadine, their pharmaceutically acceptable salts and mixtures thereof.
  • the expectorants (also known as mucolytic agents) useful in the present invention include glyceryl guaiacolate, terpin hydrate, ammonium chloride, N-acetylcysteine and bromhexine, ambroxol, their pharmaceutically acceptable salts, and mixtures thereof. All of these components, as well as their acceptable dosage ranges are described in the following: U.S. Patent 4,783,465 to Sunshine et al., is ⁇ sued November 8, 1988, U.S. Patent 4,619,934 to Sunshine et al., issued October 28, 1986, which are incorporated by reference herein. Additional agents which are found useful in the present compositions are ⁇ -agonists such as those disclosed in U.S. Patent 5,478,858, issued December 26, 1995, incorporated herein by reference in its entirety.
  • oral dosage forms can be used, including such solid forms as tablets, caplets, capsules, granules, lozenges and bulk powders and liquid forms such as syr- ups and suspensions. Controlled release dosage forms which provide a controlled release of these activ ) are also useful. These oral forms comprise a safe and effective amount, usually at least about 5% of the active components.
  • Solid oral dosage forms preferably contain from about 5% to about 95%, more preferably from about 10% to about 95%, and most preferably from about 25% to about 95% ofthe active components.
  • Liquid oral dosage forms preferably contain from about 1% to about 50% and more preferably from about 1% to about 25% and most preferably from about 3% to about 10% ofthe active components.
  • Tablets can be compressed, triturated, enteric-coated, sugar-coated, film-coated or multiple compressed, containing suitable binders, lubricants, diluents, disintegrating agents, coloring agents, flavoring agents, preservatives and flow- inducing agents. Also useful are soft gelatin capsules.
  • Liquid oral dosage forms include aqueous and nonaqueous solutions, emul ⁇ sions, pseudo emulsions, suspensions, and solutions and/or suspensions recons ⁇ tituted from non-effervescent granules, containing suitable solvents, preservatives, emulsifying agents, suspending agents, diluents, sweeteners, taste-masking agents, coloring agents, and flavoring agents.
  • suitable solvents preservatives, emulsifying agents, suspending agents, diluents, sweeteners, taste-masking agents, coloring agents, and flavoring agents.
  • Specific examples of pharmaceutically ac ⁇ ceptable carriers and excipients that may be used to formulate oral dosage forms, are described in U.S. Patent 3,903,297, Robert, issued September 2, 1975, incorpo ⁇ rated by reference herein.
  • caffeine An additional agent found useful in the present compositions is caffeine.
  • Caffeine has been found to lessen the sedating effect of the pyrrolidine and piperidine ethers.
  • the level of caffeine use is generally from about 20 mg to about 500 mg, preferably from about 50 mg to about 200 mg, most preferably from about 65 mg to about 100 mg.
  • the active component is incor- porated into an aqueous-based orally acceptable pharmaceutical carrier consistent with conventional pharmaceutical practices.
  • An "aqueous-based orally acceptable pharmaceutical carrier” is one wherein the entire or predominant solvent content is water.
  • Typical carriers include simple aqueous solutions, syrups, dispersions and suspensions, and aqueous based emulsions such as the oil-in-water type.
  • the most preferred carrier is a suspension of the pharmaceutical composition in an aqueous vehicle containing a suitable suspending agent.
  • Suitable suspending agents include Avicel RC-591 (a microcrystalline-cellulose/sodium carboxymethyl cellulose mix ⁇ ture available from FMC), guar gum and the like. Such suspending agents are well known to those skilled in the art.
  • the total water content based on the weight of the final composition, will generally range from about 20 to about 75%, and, preferably, from about 20 to about 40%, by weight/volume.
  • typical liquid formu ⁇ lations preferably contain a co-solvent, for example, propylene glycol, glycerin, sor ⁇ bitol solution and the like, to assist solubilization and incorporation of water-insoluble ingredients, such as flavoring oils and the like into the composition.
  • compositions of this invention preferably contain from about 5 to about 25 volume/volume percent and, most preferably, from about 10 to about 25 volume/ volume percent, ofthe co-solvent.
  • Other optional ingredients well known to the pharmacist's art may also be included in amounts generally known for these ingredients, for example, natural or artificial sweeteners, flavoring agents, colorants and the like to provide a palatable and pleasant looking final product, antioxidants, for example, butylated hydroxy ani- sole or butylated hydroxy toluene, and preservatives, for example, methyl or propyl paraben or sodium benzoate, to prolong and enhance shelf life.
  • a highly preferred optional component is caffeine.
  • the amount ofthe pharmaceutical composition administered depends upon the percent of active ingredients within its formula, which is a function of the amount of the naphthalene derivative and any optional components such as a de- congestant, cough suppressant, expectorant and/or antihistamine required per dose, stability, release characteristics and other pharmaceutical parameters.
  • each individual dosage ofthe pharmaceutical com- positions of the present invention range from about 1 mg/kg to about 25 mg/kg, preferably from about 2 mg/kg to about 15 mg/kg and most preferably from about 3 mg/kg to about 10 mg/kg.
  • a hard gelatin capsule composition for oral administration is prepared by combining the following ingredients: Ingredient Amount
  • Triturate active ingredients and q.s. with lactose to selected capsule size are administered to selected capsule size.
  • Administration of one or two the above capsules every four to twelve hours to a human in need of treatment provides improved relief from cough, cold-like, flu, flu-like and allergic rhinitis symptoms.
  • EXAMPLE ⁇ A hard compressed caplet composition for oral administration is prepared by combining the following ingredients:
  • AdiTiinistration of two caplets every twelve hours to a human in need of treatment provides improved relief from cough, cold-like, flu-like and allergic rhinitis symptoms.
  • a hard compressed tablet composition for oral administration is prepared by combining the following ingredients:
  • Administration of one ofthe above tablets every twelve hours to a human in need of treatment provides improved relief from cough, cold-like, flu, flu-like and allergic rhinitis symptoms.
  • a liquid composition for oral administration is prepared by combining the following ingredients:
  • the purified water (approximately 10% ofthe final batch volume) is poured into a batch container equipped with a lightnin' mixer.
  • the sodium citrate, citric acid, and actives other than naproxen sodium are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then added.
  • the colorants are added to purified water (approximately 0.5% ofthe final batch volume). This colorant solution is then added to the first batch container.
  • the naproxen sodium is added to the alcohol while stirring.
  • the propylene glycol and flavors are added to this alcohol premix and the resulting mixture is stirred until homogeneous and then added to the first container.
  • the remaining purified water is added to the resulting mixture and stirred.
  • a liquid composition for oral administration is prepared by combining the following ingredients:
  • the purified water (approximately 10% ofthe final batch volume) is poured into a batch container equipped with a lightnin' mixer.
  • the sodium citrate, citric acid, clemastine fumarate are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then added.
  • the colorants are added to purified water (approximately 0.5% of the final batch volume). This colorant solution is then added to the first batch container.
  • the ibuprofen is added to the alcohol while stirring.
  • the propylene glycol and flavors are added to this alcohol premix and the resulting mixture is stirred until homogeneous and then added to the first container.
  • the remaining purified water is added to the resulting mixture and stirred.
  • a liquid composition for oral administration is prepared by combining the following ingredients:
  • the purified water (approximately 10% ofthe final batch volume) is poured into a batch container equipped with a lightnin' mixer.
  • the sodium citrate, citric acid and clemastine fumarate are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then added.
  • the colorants are added to purified water (approximately 0.5% ofthe final batch volume). This colorant solution is then added to the first batch container.
  • the S (+) ibuprofen lysinate and dextromethorphan HBr are added sequentially to the alcohol while stirring.
  • the propylene glycol and flavors are added to this alcohol premix and the resulting mixture is stirred until homogeneous and then added to the first container.
  • the remaining purified water is added to the resulting mixture and stirred.

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Abstract

Compositions et techniques permettant d'améliorer le traitement, le soin ou l'atténuation des rhumes, des affections du type rhume, des allergies, des symptômes touchant les sinus et/ou des symptômes de la grippe par administration d'une dose sûre et efficace d'une composition comportant un analgésique et certains antihistaminiques à base d'éthers de pyrrolidine et de pipéridine.
PCT/US1996/012249 1995-07-28 1996-07-25 Compositions contenant des analgesiques et des antihistaminiques et procedes de traitement d'affections respiratoires WO1997004808A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP9507747A JPH11510168A (ja) 1995-07-28 1996-07-25 呼吸障害を処理するための鎮痛剤及び抗ヒスタミン剤を含有する組成物及び方法
AU65991/96A AU6599196A (en) 1995-07-28 1996-07-25 Compositions containing analgesics and antihistamines and methods for treating respiratory disorders
EP96925495A EP0841947A1 (fr) 1995-07-28 1996-07-25 Compositions contenant des analgesiques et des antihistaminiques et procedes de traitement d'affections respiratoires

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US50877595A 1995-07-28 1995-07-28
US61152896A 1996-03-05 1996-03-05
US08/508,775 1996-03-05
US08/611,528 1996-03-05

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WO1997004808A1 true WO1997004808A1 (fr) 1997-02-13

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EP (1) EP0841947A1 (fr)
JP (1) JPH11510168A (fr)
AR (1) AR003470A1 (fr)
AU (1) AU6599196A (fr)
CA (1) CA2227958A1 (fr)
CO (1) CO4750820A1 (fr)
PE (1) PE12098A1 (fr)
WO (1) WO1997004808A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032586A1 (fr) * 1996-03-05 1997-09-12 The Procter & Gamble Company Utilisation de la cafeine et de la clemastine pour le traitement de troubles respiratoires
WO1998042322A3 (fr) * 1997-03-26 1998-12-17 Dezso Korbonits Compositions antitussives
WO1999015173A1 (fr) * 1997-09-19 1999-04-01 The Procter & Gamble Company Compositions et procedes de traitement de troubles respiratoires
EP0956014A4 (fr) * 1996-11-13 2001-03-07 Nastech Pharm Co Procede destine a ameliorer la solubilite de la clemastine et compositions pharmaceutiques a base d'une telle clemastine
WO2005074885A1 (fr) * 2004-02-03 2005-08-18 Philippe Perovitch Procede de diffusion de molecules insolubles en milieu aqueux et composition mettant en oeuvre ce procede
US7014867B2 (en) 2001-06-28 2006-03-21 Ucb Farchim Sa Tablet comprising cetirizine and pseudoephedrine
EA008765B1 (ru) * 2004-11-22 2007-08-31 Закрытое Акционерное Общество «Научно-Производственное Объединение "Антивирал"» (Зао «Нпо "Антивирал"») Антигриппозное средство
EP1437134A4 (fr) * 2001-09-04 2009-03-11 Boehringer Ingelheim Int Medicament contre la grippe de type a
US7863287B2 (en) 2002-12-18 2011-01-04 Wyeth Llc Compositions of non-steroidal anti-inflammatory drugs, decongestants and anti-histamines

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Publication number Priority date Publication date Assignee Title
JP5598108B2 (ja) * 2009-07-09 2014-10-01 ライオン株式会社 内服用固形組成物

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EP0130690A2 (fr) * 1983-06-01 1985-01-09 Teijin Limited Préparation pharmaceutique pour guérir les maladies du périoste dentaire et procédé de sa fabrication
WO1985004589A1 (fr) * 1984-04-09 1985-10-24 Abraham Sunshine Melanges contre la toux et le rhume comprenant des medicaments anti-inflammatoires non steraniques
WO1992005783A1 (fr) * 1990-09-28 1992-04-16 Merck & Co., Inc. Combinaisons d'ibuprofene-antihistamine
WO1993009764A1 (fr) * 1991-11-19 1993-05-27 Center For Innovative Technology Traitement des rhumes a l'aide d'une therapie associant des agents antimediatiques et virostatiques (covam)
WO1994009767A1 (fr) * 1992-10-31 1994-05-11 Smithkline Beecham Plc Nouvelle utilisation de compositions pharmaceutiques
WO1994014449A1 (fr) * 1992-12-21 1994-07-07 The Procter & Gamble Company Compositions contenant de la cafeine et s(+)-ibuprofene ou s(+)-flurbiprofene ou s(+)-cetoprofene

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EP0130690A2 (fr) * 1983-06-01 1985-01-09 Teijin Limited Préparation pharmaceutique pour guérir les maladies du périoste dentaire et procédé de sa fabrication
WO1985004589A1 (fr) * 1984-04-09 1985-10-24 Abraham Sunshine Melanges contre la toux et le rhume comprenant des medicaments anti-inflammatoires non steraniques
WO1992005783A1 (fr) * 1990-09-28 1992-04-16 Merck & Co., Inc. Combinaisons d'ibuprofene-antihistamine
WO1993009764A1 (fr) * 1991-11-19 1993-05-27 Center For Innovative Technology Traitement des rhumes a l'aide d'une therapie associant des agents antimediatiques et virostatiques (covam)
WO1994009767A1 (fr) * 1992-10-31 1994-05-11 Smithkline Beecham Plc Nouvelle utilisation de compositions pharmaceutiques
WO1994014449A1 (fr) * 1992-12-21 1994-07-07 The Procter & Gamble Company Compositions contenant de la cafeine et s(+)-ibuprofene ou s(+)-flurbiprofene ou s(+)-cetoprofene

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032586A1 (fr) * 1996-03-05 1997-09-12 The Procter & Gamble Company Utilisation de la cafeine et de la clemastine pour le traitement de troubles respiratoires
EP0956014A4 (fr) * 1996-11-13 2001-03-07 Nastech Pharm Co Procede destine a ameliorer la solubilite de la clemastine et compositions pharmaceutiques a base d'une telle clemastine
WO1998042322A3 (fr) * 1997-03-26 1998-12-17 Dezso Korbonits Compositions antitussives
US6348470B1 (en) 1997-03-26 2002-02-19 Korbonits Dezsoe Antitussive compositions
WO1999015173A1 (fr) * 1997-09-19 1999-04-01 The Procter & Gamble Company Compositions et procedes de traitement de troubles respiratoires
US7014867B2 (en) 2001-06-28 2006-03-21 Ucb Farchim Sa Tablet comprising cetirizine and pseudoephedrine
US7226614B2 (en) 2001-06-28 2007-06-05 Ucb Farchim Sa Tablet comprising cetirizine and pseudoephedrine
EP1437134A4 (fr) * 2001-09-04 2009-03-11 Boehringer Ingelheim Int Medicament contre la grippe de type a
US7863287B2 (en) 2002-12-18 2011-01-04 Wyeth Llc Compositions of non-steroidal anti-inflammatory drugs, decongestants and anti-histamines
WO2005074885A1 (fr) * 2004-02-03 2005-08-18 Philippe Perovitch Procede de diffusion de molecules insolubles en milieu aqueux et composition mettant en oeuvre ce procede
US8846083B2 (en) 2004-02-03 2014-09-30 Philippe Perovitch Method for the diffusion of molecules which are insoluble in an aqueous medium and composition using said method
EA008765B1 (ru) * 2004-11-22 2007-08-31 Закрытое Акционерное Общество «Научно-Производственное Объединение "Антивирал"» (Зао «Нпо "Антивирал"») Антигриппозное средство

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CO4750820A1 (es) 1999-03-31
CA2227958A1 (fr) 1997-02-13
AR003470A1 (es) 1998-08-05
EP0841947A1 (fr) 1998-05-20
JPH11510168A (ja) 1999-09-07
AU6599196A (en) 1997-02-26
PE12098A1 (es) 1998-04-19

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